Homes for Sale in 53575

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  /29

  $1,250,000

  • 5 Beds
  • 6 Baths
  • 5,729 Sq Ft

  670 Inverness St, Oregon, WI 53575

  Freshly painted and move-in ready, this extraordinary 5-bedroom, 6-bathroom custom home offers true resort-style living on the 10th hole at The Legends at Bergamont. Blending elegance with everyday comfort, it’s designed for both relaxed living and unforgettable entertaining. Inside you’ll love the updated chef’s kitchen, spacious living room with a custom entertainment center, dedicated home

  

  Sarah Gabrielse

  Devout Real Estate Group, LLC

  (608) 420-5980

  670 Inverness St, Oregon, WI 53575
• 

  

  

  /20

  $2,550,000

  • 4 Beds
  • 1.5 Baths
  • 2,628 Sq Ft

  4890 County Road A, Oregon, WI 53575

  34 beautiful acres right outside of the Village of Oregon, hemmed in by parks and greenspace. With hardwood floors, the original mid-century styled kitchen and study, radiant heat, geothermal, and efficiency upgrades, add some cosmetic touches and the property will stand out! With mineral rights below the soil and the potential for alternate uses of the property in the future, this is one to

  

  Jean Armendariz-Kerr

  Mode Realty Network

  (608) 344-6238

  4890 County Road A, Oregon, WI 53575
• 

  

  

  /7

  $3,750,000

  • Land
  • 20 Acres
  • $187,500 per Acre

  5431 Lincoln Rd, Oregon, WI 53575

  Prime development opportunity! This property on Lincoln Rd offers exceptional potential for builders and investors with ample acreage and convenient access to Hwy 14 and Hwy M. Ideally located near the new Library, Post Office, Bergamont Subdivision, and directly across from holes 13 and 14 of The Legend at Bergamont Golf Course, the site is perfectly positioned for a new subdivision,

  

  Allen Morris

  Berkshire Hathaway HomeServices True Realty

  (608) 691-6330

  5431 Lincoln Rd, Oregon, WI 53575
• 

  

  

  /36

  $500,000

  • 3 Beds
  • 3 Baths
  • 2,880 Sq Ft

  402 Concord Dr, Oregon, WI 53575

  Rare propertunity with golf course views, extra parcel for expanded side yard, 3rd and 4th bedroom options in the Oregon School District. This ranch has the master bedroom on the main floor with a 2nd master suite in the lower level. Cooks’ kitchen offers enough space for all your favorite kitchen gadgets and space to prep for parties. Formal dining room flows into the living room with fireplace

  

  Jason McGill

  KJK & Associates, LLC

  (608) 820-0572

  402 Concord Dr, Oregon, WI 53575
• 

  

  

  /20

  $559,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,723 Sq Ft

  Rutherford II Plan at Highlands of Netherwood, Oregon, WI 53575

  This new single-story home provides the convenience of having everything laid out on one level. It features an open design among the living room, dining room and kitchen, which has a large center island. The covered front porch and back patio enhance outdoor enjoyment. Included are two secondary bedrooms and an owner’s suite tucked in a back corner of the home for privacy.

  

  Lennar

  Builder

  441 Peterson Trail Unit 36033761, Oregon, WI 53575
• 

  

  /24

  $601,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,521 Sq Ft

  Townsend Plan at Highlands of Netherwood, Oregon, WI 53575

  This two-story home combines comfort with convenience. Off the foyer is a versatile flex room well-suited for hosting guests, while down the hallway is a cohesive open layout among the kitchen, dining room and family room. The second level is occupied by all four bedrooms to provide restful retreats, including the spacious owner’s suite with a private full-sized bathroom. Completing the home is a

  

  Lennar

  Builder

  441 Peterson Trail Unit 36033759, Oregon, WI 53575
• 

  

  /25

  $285,000

  • 2 Beds
  • 3.5 Baths
  • 1,967 Sq Ft

  270 Alpine Meadow Cir, Oregon, WI 53575

  Move-in ready 2 bed, 3.5 bath condo with tasteful updates throughout! Enjoy wood laminate floors, updated lighting, a cozy gas fireplace, and a kitchen with stone tile flooring, breakfast bar, tile backsplash, ample storage, and brand new dishwasher. The spacious primary suite features vaulted ceilings, a walk-in closet, and en suite bath. Second bedroom also includes its own full bath.

  Andy Kramer Redfin Corporation

  270 Alpine Meadow Cir, Oregon, WI 53575
• 

  

  /85

  $1,100,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 3,418 Sq Ft

  2127 Vintage Dr, Fitchburg, WI 53575

  This home's craftsmanship shines through in every detail. Beautifully remodeled & thoughtfully upgraded inside & out, this property sits at the end of a peaceful cul-de-sac just outside of town. The ML features a gorgeous kitchen w/ quartz countertops & custom cabinets overlooking an open concept great room w/ vaulted ceilings, perfect for entertaining. This home comes w/ plenty of leisure &

  Chris Venden Realty Executives Cooper Spransy

  2127 Vintage Dr, Fitchburg, WI 53575
• 

  

  /80

  $1,250,000

  • 4 Beds
  • 3.5 Baths
  • 4,352 Sq Ft

  1089 U S 14, Oregon, WI 53575

  Stunning 16.15-Acre Estate only 10 min to Madison. Beautifully designed 4-bed, 3.5-bth residence offers 4,300+ sq ft of living space, a 3-car attached garage, & breathtaking views of the countryside. Open-concept has a spacious kitchen that flows seamlessly into the dining area, a dramatic 2-story great room, & a bright sunroom. Step outside to a massive deck & covered porch. Upstairs, the

  Trent Estabrook Pinnacle Real Estate Group LLC

  1089 U S 14, Oregon, WI 53575
• 

  

  /36

  $449,900 Open Sun 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 2,300 Sq Ft

  168 Hickory Ct, Oregon, WI 53575

  SD 7/11. This inviting tri-level, 3 bedroom, 2 bath home feels like a private retreat nestled on a spacious lot. The open layout features hardwood floors and an impressive living area with vaulted ceilings and a striking floor-to-ceiling fireplace. Kitchen offers a breakfast bar and a newer oven, stovetop, dishwasher, microwave, and faucet. The primary bedroom has its own level with walk-in

  Cristina Daza Lauer Realty Group, Inc.

  168 Hickory Ct, Oregon, WI 53575
• 

  

  /55

  $1,099,000

  • 4 Beds
  • 4.5 Baths
  • 4,504 Sq Ft

  863 Augusta Dr, Oregon, WI 53575

  Welcome to this exquisite 2-story home boasting over 4500 square feet of thoughtfully designed living space. With 4 spacious bedrooms and 4.5 baths, this home offers an ideal blend of elegance, comfort, and functionality. Soaring vaulted ceilings and an open floor plan creates a grand atmosphere. The second-floor catwalk adds a dramatic touch, overlooking the main living area. Gourmet kitchen

  Julie Larson First Weber Inc

  863 Augusta Dr, Oregon, WI 53575
• 

  

  /23

  $663,740 New Construction

  • 4 Beds
  • 2 Baths
  • 2,639 Sq Ft

  1251 Denmark Cir, Oregon, WI 53575

  This two-story home combines modern comfort with convenience. Found off the foyer is a flex room for versatile needs, followed by a cohesive open main living area with direct access to the backyard for indoor-outdoor activities. In a private corner of the first floor is a study ideal for at-home work. Upstairs are three secondary bedrooms and the spacious owner’s suite with a full-sized bathroom.

  

  Lennar

  Builder

  1251 Denmark Cir, Oregon, WI 53575
• 

  

  /45

  $734,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,329 Sq Ft

  395 Kassander Way, Oregon, WI 53575

  Bright and airy new construction with a modern, open-concept layout designed for everyday ease and elegant entertaining. The main floor offers, gas fireplace, large pantry, mud room, and a private office for quiet work-from-home days and a covered back porch perfect for summer lounging. Upstairs, find four spacious bedrooms including a stunning ensuite with a tiled walk-in shower and walk-in

  Matt Winzenried Realty Executives Cooper Spransy

  395 Kassander Way, Oregon, WI 53575
• 

  

  /20

  $595,931 New Construction

  • 3 Beds
  • 2 Baths
  • 1,866 Sq Ft

  1214 Denmark Cir, Oregon, WI 53575

  Designed for low-maintenance living, this single-story home showcases an open-concept kitchen that overlooks the family room and dining room in an ideal set-up for seamless transitions between spaces. At the front of the home are two secondary bedrooms to provide restful retreats, while in a back corner is the private owner’s suite with a full-sized bathroom. A two-car garage offers versatile

  

  Lennar

  Builder

  1214 Denmark Cir, Oregon, WI 53575
• 

  

  /17

  $609,900 New Construction

  • 3 Beds
  • 2 Baths
  • 2,171 Sq Ft

  Ridgefield Plan at Highlands of Netherwood, Oregon, WI 53575

  This single-story home is designed to offer low-maintenance living and great space to grow. A modern open layout is situated among the large family room, kitchen and breakfast room, with an attached covered patio to offer seamless indoor-outdoor living. Found off the foyer are two secondary bedrooms, while tucked away in the back corner for maximum privacy is the sprawling owner’s suite with a

  

  Lennar

  Builder

  441 Peterson Trail Unit 36033756, Oregon, WI 53575
• 

  

  /27

  $666,900 New Construction

  • 4 - 5 Beds
  • 2.5 - 3.5 Baths
  • 2,907 Sq Ft

  Raleigh Plan at Highlands of Netherwood, Oregon, WI 53575

  A foyer leads directly into the double-height living and dining room of this two-story residence, while the family room, kitchen and breakfast area share a spacious open floorplan toward the back of the home. Ideal for at-home work is a quiet study. The top level hosts all four bedrooms, including the sprawling owner’s suite with a private full-sized bathroom and two walk-in closets for ample

  

  Lennar

  Builder

  441 Peterson Trail Unit 36033755, Oregon, WI 53575
• 

  

  /27

  $611,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,607 Sq Ft

  Wren Plan at Highlands of Netherwood, Oregon, WI 53575

  This two-story home combines modern comfort with convenience. Found off the foyer is a flex room for versatile needs, followed by a cohesive open main living area with direct access to the backyard for indoor-outdoor activities. In a private corner of the first floor is a study ideal for at-home work. Upstairs are three secondary bedrooms and the spacious owner’s suite with a full-sized bathroom.

  

  Lennar

  Builder

  441 Peterson Trail Unit 36033754, Oregon, WI 53575
• 

  

  /23

  $562,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,866 Sq Ft

  Siena II Plan at Highlands of Netherwood, Oregon, WI 53575

  Designed for low-maintenance living, this single-story home showcases an open-concept kitchen that overlooks the family room and dining room in an ideal set-up for seamless transitions between spaces. At the front of the home are two secondary bedrooms to provide restful retreats, while in a back corner is the private owner’s suite with a full-sized bathroom. A two-car garage offers versatile

  

  Lennar

  Builder

  441 Peterson Trail Unit 36033758, Oregon, WI 53575
• 

  

  /24

  $1,250,000

  • Land
  • 35 Acres
  • $35,714 per Acre

  5927 Adams Rd, Fitchburg, WI 53575

  Dream Equestrian property located just minutes from Madison! This +/-35ac ranch in Fitchburg, WI is an extremely rare find! Location is everything and it does not get better than this. The horse facilities consist of a 19 stall main barn complete with a full apartment, observation room, tack room, and indoor riding arena. A well maintained classic barn, additional storage shed, hay barn, and

  Al Weber First Weber Inc

  5927 Adams Rd, Fitchburg, WI 53575
• 

  

  /43

  $2,250,000

  • Land
  • 105 Acres
  • $21,429 per Acre

  5927 Adams Rd, Fitchburg, WI 53575

  Dream equestrian property located just minutes from Madison! This +/-105ac ranch in Fitchburg, WI is an extremely rare find! Location is everything and it does not get much better than this. The horse facilities consist of a 19 stall main barn complete with a full apartment, observation room, tack room, and indoor riding arena. A well-maintained classic barn, additional storage shed, hay barn,

  Al Weber Wildland Properties

  5927 Adams Rd, Fitchburg, WI 53575
• 

  

  /15

  $900,000

  • Land
  • 20 Acres
  • $45,000 per Acre

  0 + - 20ac Whalen Rd, Fitchburg, WI 53575

  Location Location Location! Rare opportunity to own +/- 20ac on the edge of Madison. Property is in a prime location for future development and offers potential access to both Whalen Rd and Kathleen Ln. Bring your own builder to construct your dream home with privacy and room to roam. Opportunities like this do not come up often and will likely go fast. Schedule your private showing

  Al Weber Wildland Properties

  0 + - 20ac Whalen Rd, Fitchburg, WI 53575
• 

  

  /23

  $700,000

  • 3 Beds
  • 1.5 Baths
  • 2,000 Sq Ft

  1916 County Road Mm, Fitchburg, WI 53575

  Unique investment opportunity just outside of Oregon! Check out this 6 ac parcel less than a minute off of Hwy 14, featuring a nicely maintained ranch home and over 5,000 sq ft of shop space. Multiple buildings provide a great opportunity for a wide range of rental incomes or the ideal location for a growing business. This mix of home, business and green space do not come available often.

  Al Weber Wildland Properties

  1916 County Road Mm, Fitchburg, WI 53575
• 

  

  /64

  $3,500,000

  • Land
  • 236 Acres
  • $14,831 per Acre

  +/-236 Ac Old Stone Rd, Stoughton, WI 53575

  Incredible investment opportunity in Dane County. This truly unique ~236ac property brings endless opportunities with a great mix of highly productive tillable land, lake front development opportunities and endless recreational fun! The property includes 7 build opportunities with ~3000ft of Bass Lake shoreline. Currently producing ~$45k in income between the crop and the home lease with

  Al Weber Wildland Properties

  +/-236 Ac Old Stone Rd, Stoughton, WI 53575
• 

  

  /48

  $559,900

  • 4 Beds
  • 2.5 Baths
  • 2,250 Sq Ft

  1063 Oregon Parks Ave, Oregon, WI 53575

  This contemporary 4-bedroom, 2.5-bath home in the Highlands of Netherwood offers modern style, thoughtful design, and a brilliant location. With about 2,250 sq ft of living space, the layout is open and bright—featuring a large great room that flows into a formal dining area and a walk-in pantry in the kitchen. The primary suite shines with a private bath and generous walk-in closet. Main level

  Heather Taylor MHB Real Estate

  1063 Oregon Parks Ave, Oregon, WI 53575
• 

  

  /55

  $689,000

  • 4 Beds
  • 3.5 Baths
  • 3,514 Sq Ft

  302 Oakmont St, Oregon, WI 53575

  Welcome home to this sprawling 4BR/3.5BA home in Oregon’s finest Bergamont Golf Community! Enter inside to find a well thought out and spacious floor plan featuring living room w/ cozy gas fp, formal dining, & eat-in kitchen w/ SS apps, expansive island/breakfast bar and dining area w/ walkout to your deck overlooking an amazing yard on a corner lot! Upstairs enjoy all 4 bedrooms incld. the

  Erin Flesch MHB Real Estate

  302 Oakmont St, Oregon, WI 53575
• 

  

  /69

  $745,000

  • 5 Beds
  • 3.5 Baths
  • 3,650 Sq Ft

  4795 Eisenhower St, Oregon, WI 53575

  Minutes from Oregon’s downtown, this stunning 5 bed, 3.5 bath ranch sits on a .74 mature lot. Step inside to a true wow-factor: a dramatic floor-to-ceiling stone fireplace anchoring the open-concept living area with gleaming hardwoods. The kitchen impresses with GE Cafe appliances, granite counters & maple cabinetry. Retreat to the spacious primary suite with 2 closets, soaking tub, luxury double

  Jami Erickson Realty Executives Capital City

  4795 Eisenhower St, Oregon, WI 53575
• 

  

  /40

  $585,900

  • 4 Beds
  • 3.5 Baths
  • 2,639 Sq Ft

  857 Ashworth Dr, Oregon, WI 53575

  Discover the perfect blend of modern updates and comfortable living in this spacious 2-story home! Major improvements include a brand-new roof (2025) and new AC (2021), giving you peace of mind for years to come. Step inside to a bright and inviting living room with a cozy gas fireplace. The kitchen features stainless steel appliances, a center island, and pantry, offering plenty of space for

  Kristin Shields MHB Real Estate

  857 Ashworth Dr, Oregon, WI 53575
• 

  

  /64

  $624,900

  • 4 Beds
  • 3.5 Baths
  • 2,943 Sq Ft

  826 Sumac St, Oregon, WI 53575

  Beautifully maintained 4-bedroom, 3.5-bath home in Alpine Meadows! The main level features a vaulted great room with a cozy corner gas fireplace, a spacious dining area that opens to a stunning paver patio and fenced backyard—perfect for outdoor entertaining. The kitchen offers solid surface countertops, a generous island with breakfast bar, and a large walk-in pantry. Convenient mud/laundry room

  Michael Weiss MHB Real Estate

  826 Sumac St, Oregon, WI 53575
• 

  

  /53

  $559,900

  • 4 Beds
  • 3 Baths
  • 2,333 Sq Ft

  833 Ashworth Dr, Oregon, WI 53575

  This 4 bed/3 bath bright & spacious RANCH shows well! Brand New Roof as of July 2025! Front Entry foyer leads to the spacious GR with vaulted ceiling, corner fireplace and massive windows. Well laid out kitchen with tile flooring, dark SS appliances, modern light fixtures, breakfast bar, island & pantry. Main level primary suite with vaulted ceiling, new lighting & WIC. The exposed walkout LL is

  Josh Blasi Restaino & Associates

  833 Ashworth Dr, Oregon, WI 53575
• 

  

  /22

  $574,556 New Construction

  • 4 Beds
  • 2 Baths
  • 2,249 Sq Ft

  1248 Denmark Cir, Oregon, WI 53575

  This two-story home provides modern comfort and ample room to grow. Upon entry is a flex room well-suited for hosting guests, followed by a spacious open layout for seamless family living and relaxing. Separate from the downstairs main living area, the second level hosts all four bedrooms to provide great personal space and privacy. The sprawling owner’s suite is a serene haven with a full-sized

  

  Lennar

  Builder

  1248 Denmark Cir, Oregon, WI 53575
• 

  

  /18

  $564,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,087 Sq Ft

  468 Stoddard Dr, Oregon, WI 53575

  Image is representative of home; colors may vary. All prices, promotions and specifications are subject to change at any time without notice based on the discretion of Veridian Homes.

  

  Veridian Homes

  Builder

  468 Stoddard Dr, Oregon, WI 53575
• 

  

  /34

  $564,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,092 Sq Ft

  The Everest Plan at Greenview Preserve, Oregon, WI 53575

  The Everest is one crafty home. Outside, it welcomes you like a cozy cottage. Step through the front door and it greets you more like a grand estate. To your right, a tucked-away den. Ahead, a massive great room. Off the garage, a laundry room to keep muddy boots, snowy coats and wet dogs at bay. The pleasant surprises continue with the four – four! – roomy bedrooms upstairs. And delighted smiles

  

  Veridian Homes

  Builder

  956 Merri-Hill Dr Unit 36788956, Oregon, WI 53575
• 

  

  /26

  $563,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,193 Sq Ft

  Starling Plan at Highlands of Netherwood, Oregon, WI 53575

  This two-story home provides modern comfort and ample room to grow. Upon entry is a flex room well-suited for hosting guests, followed by a spacious open layout for seamless family living and relaxing. Separate from the downstairs main living area, the second level hosts all four bedrooms to provide great personal space and privacy. The sprawling owner’s suite is a serene haven with a full-sized

  

  Lennar

  Builder

  441 Peterson Trail Unit 36033757, Oregon, WI 53575
• 

  

  /25

  $541,900 New Construction

  • 3 - 4 Beds
  • 2.5 Baths
  • 2,052 Sq Ft

  Meadowlark Plan at Highlands of Netherwood, Oregon, WI 53575

  The first level of this two-story home is host to communal spaces, including a flex space off the foyer and an open floorplan shared among the family room, dining room and kitchen. A loft and three bedrooms can be found upstairs, two of which feature walk-in closets.

  

  Lennar

  Builder

  441 Peterson Trail Unit 36033760, Oregon, WI 53575
• 

  

  /35

  $574,556 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,193 Sq Ft

  1248 Denmark Cir Unit 46, Oregon, WI 53575

  Eligible buyers may qualify for a 2/1 buy-down (10%+ down): Year 1 at 3.5%, Year 2 at 4.5%, Years 3–30 at 5.5% if closed by Nov 28, 25 with Lennar Mortgage. The Starling C Floor Plan by Lennar Homes, located on homesite #46 in the Highlands of Netherwood, will be available for move-in Nov 2025! This stunning home features upgraded Designer Select finishes throughout, including luxurious quartz

  Emily Ostermiller First Weber Inc

  1248 Denmark Cir Unit 46, Oregon, WI 53575
• 

  

  /13

  $595,931 New Construction

  • 3 Beds
  • 2 Baths
  • 1,965 Sq Ft

  1214 Denmark Cir Unit 50, Oregon, WI 53575

  The Siena B will be available for move in Jan/Feb'26. This stunning ranch home offers 3 bedrooms, 2 baths, and a thoughtfully designed layout. High-end finishes include quartz countertops, engineered hardwood flooring, stainless steel appliances, and smart home features for modern convenience. A fully landscaped yard is included, and Lennar provides added peace of mind with a 1-year workmanship

  Emily Ostermiller First Weber Inc

  1214 Denmark Cir Unit 50, Oregon, WI 53575
• 

  

  /8

  $250,000

  • 4 Beds
  • 2 Baths
  • 1,440 Sq Ft

  326 Prairie View St, Oregon, WI 53575

  Bring your vision and toolbelt and make this a great home. Home has great potential and is situated on a quiet cul de sac with less then a 10 minute walk to schools and 25 minutes south of Madison. Updates include: Metal Roof 2yrs Gutters w/gutter guards 1yr Furnace 2013 Central air 2013 Windows 2008 Great investment opportunity awaits with this property, Property being sold in As Is condition

  April Halbach First Weber Inc

  326 Prairie View St, Oregon, WI 53575
• 

  

  /85

  $1,799,900

  • 4 Beds
  • 4.5 Baths
  • 5,263 Sq Ft

  2395 White Oak Trail, Oregon, WI 53575

  One of a kind, custom built 5263 sqft home on 3 acre wooded lot w/new outbuilding offering living space & car lift. Under 10 mins south of Madison & backing to DNR & Ag land. Private 4 bed/4.5 bath house perfect for hobbyist or entertainer. Maple flrs throughout main level & into living rm w/20' vaulted clgs & custom blue magma quartz flr to clg frplc. Natural light throughout! Large 2nd living

  TC Farber RE/MAX Preferred

  2395 White Oak Trail, Oregon, WI 53575
• 

  

  /90

  $1,550,000

  • 6 Beds
  • 4.5 Baths
  • 5,519 Sq Ft

  1329 County Road D, Oregon, WI 53575

  Escape to your own private oasis at 1329 County Road D in Oregon, WI. Set on a sprawling, picturesque lot just minutes from Madison and EPIC, this spacious home offers refinished hardwood floors, updated utilities, newer roof, gutters, and HVAC. The backyard is an entertainer’s dream with an in-ground pool and lush surroundings perfect for relaxing or gathering with friends. A massive

  Aaron Weber Compass Real Estate Wisconsin

  1329 County Road D, Oregon, WI 53575
• 

  

  /53

  $385,000 Open Fri 4PM - 6PM

  • 3 Beds
  • 2 Baths
  • 1,454 Sq Ft

  126 Thomson Ln, Oregon, WI 53575

  Welcome to this stunning 3 bed, 2 bath ranch home featuring soaring vaulted ceilings and abundant natural light throughout. The gourmet kitchen is equipped with high-end appliances, custom cabinetry, and a stylish backsplash, perfect for both everyday living and entertaining. The spacious primary suite offers a private retreat with a stand-up shower, while zero-entry access adds ease and

  Areal Guenther Realty Executives Cooper Spransy

  126 Thomson Ln, Oregon, WI 53575

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